Dear SaaStr: How Common Is It For a Seed Investor To Have The Right to Block a Sale? It’s not super common to have an explicit “veto”, but it’s not unheard of either. Usually it’s phrased as a consent by the investors rather than a veto. And...
We’re back on 20VC+SaaStr, and its a great one as Canva Co-Founder and COO Cliff Obrecht joins Harry, Rory and Jason for a deep dive into this week’s biggest venture deals, AI infrastructure spending, and the return of public SaaS valuations. And why...
Dear SaaStr: I am a candidate for a VP Sales job. What are great questions to ask the CEO? I’m involved at any given time with 2-3 VP of Sales and CROs searches across SaaStr Fund portfolio companies. One thing is common across all of them: I am shocked how...
Dear SaaStr: What Should I Look For In My Very First Sales Rep? The first thing to understand is that hiring your first sales rep is one of the most critical decisions you’ll make. It’s not just about finding someone who can sell—it’s about finding someone who can...
How do you know if a B2B start-up counts as an "AI" start-up? Answer: if it's growing at insane rates Then it counts — Jason ✨👾SaaStr.Ai✨ Lemkin (@jasonlk) September 4, 2025 The data doesn’t lie. But the story is more complex than “SaaS...
OK Summer is over. That means it’s time to step it up even harder: – Have you been dragging your feet on letting that VP go … that never hit plan?– Are releases … not really going out any faster?– Is the competition pulling even … or even ahead …...
Marc Benioff just provided the ultimate proof point for AI SDRs during his appearance on 20VC+SaaStr: Salesforce has used AI agents to being to tackle 100 million uncontacted leads accumulated over 26 years. 100,000,000. “We just have not had the people,”...
Dear SaaStr: I run a 30M arr software company — operating as both CEO and CRO. I feel like I failing at both – what is a better option? At $30M ARR, you’re at a stage where the demands of both the CEO and CRO roles are too significant for one person to handle...
Some of our most compelling B2B and SaaS founders built their companies from deep domain expertise. Others stumbled into their markets … almost by accident. In the middle, some sort of knew their space, but the journey was an entirely new one. Which is better...
A deep dive from the founder/CEO of FlatFile, building AI agents for enterprise data preparation in highly sensitive environments. And come meet Flatfile at 2026 SaaStr Annual + AI Summit, they’ll be back! May 12-14 in SF Bay!! I’m David Boskovic, the...
